There are plenty of reasons to trade guarantees for maybes, like when the guaranteed thing is something you already have in abundance, and the maybe is something you ostensibly value quite highly and would reasonably want to increase your odds of acquiring.
And your framing of this remains disingenuous. Again, it's not:
Money + decreased probability of positive fan reception
vs.
No money + increased probability of positive fan reception
It's:
A f***load of money + decreased probability of positive fan reception
vs.
A marginally smaller f***load of money + increased probability of positive fan reception
If you're an already rich person (who is about to become substantially richer no matter what) who is also quite affected by what people think of you and you still choose the former option, you're stupid (and/or greedy) in a way that defies description.
And not for nothing, but you know we're posting on a hockey forum right now, yeah? Trading guarantees for maybes literally happens multiple times a year, every year. Like there's a whole day dedicated to general managers and the media making a spectacle of exactly that. Average people take the day off work to ensure they don't miss it. Someone should've told David Poile to not trade a guarantee for a maybe when he traded Martin Erat for Filip Forsberg. The idea that "you don't trade guarantees for maybes" is demonstrably false.
This conversation might be getting too abstract.